1-(2-Methoxyphenyl)piperazine → HCID 10202244, compound

HRID 1066057Notes

Reaction equation

HRID 1066057 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH2:23]([C:30]1[N:31]=[C:32]([C:37]([CH3:40])([CH3:39])[CH3:38])[O:33][C:34]=1[CH2:35]Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CC(C)=O>[CH2:23]([C:30]1[N:31]=[C:32]([C:37]([CH3:40])([CH3:39])[CH3:38])[O:33][C:34]=1[CH2:35][N:12]1[CH2:13][CH2:14][N:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[CH2:10][CH2:11]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 13461-(2-Methoxyphenyl)piperazineHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 21197965HCID 21197965, compound

Product 1

HCID 10202244HCID 10202244, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension containing 2-methoxyphenylpiperazine (1.0 mmole), potassium carbonate (2.0 mmole), potassium iodide (0.5 mmole) and 4-benzyl-5-chloromethyl-2-tertbutyl oxazole (1.0 mmole) from example 4, was stirred in acetone (10 ml) at ambient temperature for three days. The solvent was removed in vacuo, water (50 ml) added and the product extracted into ethyl acetate (3×50 ml). The combined organics were washed with water (50 ml), dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The product was purified by “flash” chromatography over silica gel to afford the titled compound as a colorless oil (0.64 mmole, 64% yield). This was transformed into its mono-fumarate salt, a white crystalline powder, using the procedure outlined in example 10 above.

Workup

  1. customThe solvent was removed in vacuo, water (50 ml)
  2. additionadded
  3. extractionthe product extracted into ethyl acetate (3×50 ml)
  4. washThe combined organics were washed with water (50 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by “flash” chromatography over silica gel

Sources & evidence

ORD record
ord-91e3e41691e443fe92152a890cfe915a
Source dataset
uspto-grants-2001_06
Patent number
US06242448B1

Reaction notes

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